3,4-Dihydroxy-benzaldehyde thio-semi-carbazone.

The asymmetric unit of the title compound, C(8)H(9)N(3)O(2)S, contains three independent mol-ecules which are stacked approximately over each other. In the crystal structure, centrosymmetric pairs of mol-ecules are formed through inter-molecular hydr-oxy-hydr-oxy O-H⋯O and hydr-oxy-sulfur O-H⋯S hydrogen bonds which are, in turn, linked into a two-dimensional network by N-H⋯O(hydr-oxy) hydrogen bonds.

Related literature

For the structure of 3,4-dihydroxy­benzaldehyde 4-phenyl­thio­semicarbazone, see: Swesi et al. (2006 ▶). For some metal complexes of the ligand, see: Zhu et al. (1991 ▶, 1997 ▶).

Experimental

Crystal data

C8H9N3O2S

M = 211.24

Triclinic,

a = 10.657 (2) Å

b = 11.794 (2) Å

c = 12.356 (2) Å

α = 111.657 (2)°

β = 104.082 (2)°

γ = 90.929 (2)°

V = 1390.2 (4) Å3

Z = 6

Mo Kα radiation

μ = 0.33 mm−1

T = 100 (2) K

0.20 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.938, T max = 0.987

8792 measured reflections

6298 independent reflections

3727 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.189

S = 1.01

6298 reflections

397 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801386X/lh2626sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801386X/lh2626Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H9N3O2S	Z = 6
Mr = 211.24	F000 = 660
Triclinic, P1	Dx = 1.514 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.657 (2) Å	Cell parameters from 1478 reflections
b = 11.794 (2) Å	θ = 2.7–27.8º
c = 12.356 (2) Å	µ = 0.33 mm−1
α = 111.657 (2)º	T = 100 (2) K
β = 104.082 (2)º	Block, yellow
γ = 90.929 (2)º	0.20 × 0.18 × 0.04 mm
V = 1390.2 (4) Å3

Bruker SMART APEX diffractometer	6298 independent reflections
Radiation source: fine-focus sealed tube	3727 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.938, Tmax = 0.987	k = −15→9
8792 measured reflections	l = −14→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.1004P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
6298 reflections	Δρmax = 0.51 e Å−3
397 parameters	Δρmin = −0.39 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
S1	0.84547 (10)	0.94314 (8)	0.21803 (8)	0.0401 (3)
S2	0.45653 (10)	0.85179 (8)	0.31556 (7)	0.0359 (2)
S3	0.10237 (10)	0.74686 (8)	0.41416 (8)	0.0390 (3)
O1	0.7414 (3)	0.5896 (2)	0.7057 (2)	0.0440 (7)
H1O	0.750 (4)	0.566 (4)	0.763 (3)	0.066*
O2	0.7519 (2)	0.7405 (2)	0.9368 (2)	0.0333 (6)
H2O	0.769 (4)	0.797 (3)	1.0057 (17)	0.050*
O3	0.4715 (4)	0.5066 (2)	0.8312 (2)	0.0615 (9)
H3O	0.476 (5)	0.496 (5)	0.895 (3)	0.092*
O4	0.4659 (3)	0.6536 (2)	1.05646 (19)	0.0359 (6)
H4O	0.464 (4)	0.710 (3)	1.122 (2)	0.054*
O5	0.2270 (3)	0.4329 (2)	0.9629 (2)	0.0441 (7)
H5O	0.232 (4)	0.426 (4)	1.029 (2)	0.066*
O6	0.1658 (3)	0.5600 (2)	1.1704 (2)	0.0370 (6)
H6O	0.152 (4)	0.609 (3)	1.235 (2)	0.056*
N1	0.7685 (3)	0.7537 (3)	0.2628 (2)	0.0407 (8)
H1N1	0.7486	0.7210	0.3109	0.049*
H1N2	0.7622	0.7072	0.1868	0.049*
N2	0.8145 (3)	0.9368 (2)	0.4209 (2)	0.0328 (7)
H2N	0.8332	1.0172	0.4520	0.039*
N3	0.7922 (3)	0.8755 (2)	0.4912 (2)	0.0316 (6)
N4	0.4570 (3)	0.6598 (3)	0.3786 (3)	0.0438 (8)
H4N1	0.4531	0.6259	0.4305	0.053*
H4N2	0.4637	0.6141	0.3061	0.053*
N5	0.4424 (3)	0.8421 (2)	0.5209 (2)	0.0294 (6)
H5N	0.4379	0.9218	0.5460	0.035*
N6	0.4390 (3)	0.7808 (2)	0.5960 (2)	0.0282 (6)
N7	0.1429 (3)	0.5636 (3)	0.4892 (3)	0.0470 (9)
H7N1	0.1457	0.5309	0.5431	0.056*
H7N2	0.1607	0.5210	0.4205	0.056*
N8	0.0866 (3)	0.7341 (3)	0.6182 (2)	0.0334 (7)
H8N	0.0617	0.8082	0.6370	0.040*
N9	0.1000 (3)	0.6760 (2)	0.6982 (2)	0.0299 (6)
C1	0.8075 (3)	0.8720 (3)	0.3043 (3)	0.0300 (7)
C2	0.7942 (3)	0.9415 (3)	0.5994 (3)	0.0306 (7)
H2	0.8072	1.0284	0.6258	0.037*
C3	0.7772 (3)	0.8876 (3)	0.6840 (3)	0.0279 (7)
C4	0.7636 (3)	0.7614 (3)	0.6542 (3)	0.0296 (7)
H4	0.7605	0.7070	0.5743	0.035*
C5	0.7545 (3)	0.7147 (3)	0.7389 (3)	0.0293 (7)
C6	0.7597 (3)	0.7934 (3)	0.8565 (3)	0.0257 (7)
C7	0.7714 (3)	0.9180 (3)	0.8871 (3)	0.0319 (8)
H7C	0.7737	0.9719	0.9670	0.038*
C8	0.7799 (3)	0.9652 (3)	0.8013 (3)	0.0327 (8)
H8	0.7875	1.0516	0.8228	0.039*
C9	0.4526 (3)	0.7787 (3)	0.4095 (3)	0.0273 (7)
C10	0.4204 (3)	0.8443 (3)	0.6983 (3)	0.0288 (7)
H10	0.4054	0.9277	0.7164	0.035*
C11	0.4218 (3)	0.7917 (3)	0.7876 (3)	0.0252 (7)
C12	0.4409 (3)	0.6698 (3)	0.7657 (3)	0.0298 (7)
H12	0.4459	0.6164	0.6879	0.036*
C13	0.4526 (3)	0.6261 (3)	0.8557 (3)	0.0321 (8)
C14	0.4480 (3)	0.7039 (3)	0.9711 (3)	0.0257 (7)
C15	0.4243 (3)	0.8234 (3)	0.9921 (3)	0.0316 (8)
H15	0.4172	0.8760	1.0694	0.038*
C16	0.4107 (3)	0.8671 (3)	0.9006 (3)	0.0304 (7)
H16	0.3936	0.9495	0.9153	0.036*
C17	0.1122 (3)	0.6761 (3)	0.5111 (3)	0.0306 (7)
C18	0.0760 (3)	0.7363 (3)	0.7984 (3)	0.0286 (7)
H18	0.0465	0.8147	0.8120	0.034*
C19	0.0928 (3)	0.6872 (3)	0.8926 (3)	0.0264 (7)
C20	0.1458 (3)	0.5772 (3)	0.8812 (3)	0.0288 (7)
H20	0.1662	0.5295	0.8081	0.035*
C21	0.1686 (3)	0.5376 (3)	0.9745 (3)	0.0291 (7)
C22	0.1375 (3)	0.6051 (3)	1.0814 (3)	0.0270 (7)
C23	0.0804 (3)	0.7116 (3)	1.0922 (3)	0.0295 (7)
H23	0.0556	0.7566	1.1637	0.035*
C24	0.0594 (3)	0.7524 (3)	0.9982 (3)	0.0300 (7)
H24	0.0214	0.8264	1.0064	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0718 (7)	0.0287 (5)	0.0288 (5)	0.0104 (4)	0.0234 (4)	0.0146 (4)
S2	0.0636 (6)	0.0242 (4)	0.0253 (4)	0.0079 (4)	0.0172 (4)	0.0123 (4)
S3	0.0631 (6)	0.0330 (5)	0.0286 (5)	0.0124 (4)	0.0187 (4)	0.0164 (4)
O1	0.083 (2)	0.0205 (12)	0.0354 (14)	0.0112 (13)	0.0242 (14)	0.0123 (11)
O2	0.0527 (15)	0.0269 (13)	0.0263 (12)	0.0067 (11)	0.0144 (11)	0.0144 (10)
O3	0.137 (3)	0.0278 (15)	0.0344 (15)	0.0361 (17)	0.0385 (18)	0.0173 (13)
O4	0.0637 (17)	0.0257 (13)	0.0238 (12)	0.0131 (12)	0.0166 (12)	0.0123 (10)
O5	0.083 (2)	0.0266 (13)	0.0343 (14)	0.0200 (13)	0.0278 (14)	0.0167 (12)
O6	0.0633 (17)	0.0276 (13)	0.0252 (12)	0.0146 (12)	0.0162 (12)	0.0127 (11)
N1	0.075 (2)	0.0255 (16)	0.0245 (15)	0.0053 (15)	0.0198 (15)	0.0091 (13)
N2	0.0565 (19)	0.0214 (14)	0.0249 (14)	0.0070 (13)	0.0161 (13)	0.0105 (12)
N3	0.0492 (18)	0.0255 (15)	0.0270 (14)	0.0069 (13)	0.0133 (13)	0.0156 (12)
N4	0.085 (3)	0.0232 (16)	0.0285 (16)	0.0122 (16)	0.0230 (16)	0.0106 (13)
N5	0.0500 (18)	0.0194 (13)	0.0235 (14)	0.0081 (12)	0.0140 (12)	0.0107 (11)
N6	0.0444 (17)	0.0221 (14)	0.0230 (13)	0.0032 (12)	0.0105 (12)	0.0131 (11)
N7	0.088 (3)	0.0285 (17)	0.0371 (17)	0.0156 (17)	0.0319 (17)	0.0165 (14)
N8	0.0529 (19)	0.0271 (15)	0.0302 (15)	0.0141 (13)	0.0172 (13)	0.0179 (13)
N9	0.0426 (17)	0.0239 (14)	0.0293 (14)	0.0056 (12)	0.0133 (12)	0.0147 (12)
C1	0.043 (2)	0.0262 (17)	0.0261 (17)	0.0123 (15)	0.0121 (15)	0.0143 (15)
C2	0.044 (2)	0.0221 (16)	0.0274 (17)	0.0042 (15)	0.0093 (15)	0.0119 (14)
C3	0.0387 (19)	0.0247 (17)	0.0249 (16)	0.0075 (14)	0.0106 (14)	0.0134 (14)
C4	0.042 (2)	0.0221 (16)	0.0261 (17)	0.0081 (14)	0.0122 (14)	0.0087 (14)
C5	0.0412 (19)	0.0190 (16)	0.0316 (17)	0.0082 (14)	0.0128 (15)	0.0119 (14)
C6	0.0326 (18)	0.0267 (17)	0.0235 (16)	0.0092 (14)	0.0116 (13)	0.0132 (14)
C7	0.050 (2)	0.0246 (17)	0.0223 (16)	0.0063 (15)	0.0118 (15)	0.0086 (14)
C8	0.049 (2)	0.0179 (16)	0.0316 (18)	0.0037 (15)	0.0121 (16)	0.0094 (14)
C9	0.0363 (18)	0.0234 (17)	0.0245 (16)	0.0080 (14)	0.0089 (14)	0.0111 (14)
C10	0.0357 (19)	0.0256 (17)	0.0293 (17)	0.0079 (14)	0.0114 (14)	0.0137 (14)
C11	0.0315 (17)	0.0240 (16)	0.0250 (16)	0.0059 (13)	0.0099 (13)	0.0133 (14)
C12	0.046 (2)	0.0250 (17)	0.0211 (15)	0.0092 (15)	0.0134 (14)	0.0092 (14)
C13	0.050 (2)	0.0209 (16)	0.0306 (17)	0.0120 (15)	0.0156 (15)	0.0126 (14)
C14	0.0371 (18)	0.0245 (16)	0.0211 (15)	0.0062 (14)	0.0111 (13)	0.0128 (13)
C15	0.047 (2)	0.0236 (17)	0.0259 (17)	0.0085 (15)	0.0163 (15)	0.0074 (14)
C16	0.048 (2)	0.0191 (16)	0.0296 (17)	0.0078 (14)	0.0133 (15)	0.0132 (14)
C17	0.0397 (19)	0.0259 (17)	0.0288 (17)	0.0040 (15)	0.0122 (15)	0.0116 (15)
C18	0.0333 (18)	0.0267 (17)	0.0289 (17)	0.0061 (14)	0.0096 (14)	0.0131 (14)
C19	0.0337 (18)	0.0221 (16)	0.0242 (16)	0.0019 (13)	0.0079 (13)	0.0098 (13)
C20	0.042 (2)	0.0212 (16)	0.0262 (16)	0.0048 (14)	0.0140 (14)	0.0094 (14)
C21	0.0408 (19)	0.0205 (16)	0.0300 (17)	0.0070 (14)	0.0141 (14)	0.0111 (14)
C22	0.0361 (18)	0.0240 (16)	0.0242 (16)	0.0036 (14)	0.0103 (14)	0.0115 (14)
C23	0.0405 (19)	0.0252 (17)	0.0245 (16)	0.0092 (15)	0.0131 (14)	0.0084 (14)
C24	0.0375 (19)	0.0248 (17)	0.0281 (17)	0.0067 (14)	0.0089 (14)	0.0103 (14)

S1—C1	1.693 (3)	N9—C18	1.270 (4)
S2—C9	1.689 (3)	C2—C3	1.453 (4)
S3—C17	1.680 (3)	C2—H2	0.9500
O1—C5	1.372 (4)	C3—C4	1.391 (4)
O1—H1O	0.837 (10)	C3—C8	1.393 (4)
O2—C6	1.369 (4)	C4—C5	1.372 (4)
O2—H2O	0.840 (10)	C4—H4	0.9500
O3—C13	1.358 (4)	C5—C6	1.392 (4)
O3—H3O	0.836 (10)	C6—C7	1.371 (4)
O4—C14	1.367 (4)	C7—C8	1.387 (4)
O4—H4O	0.841 (10)	C7—H7C	0.9500
O5—C21	1.368 (4)	C8—H8	0.9500
O5—H5O	0.838 (10)	C10—C11	1.450 (4)
O6—C22	1.364 (4)	C10—H10	0.9500
O6—H6O	0.844 (10)	C11—C16	1.385 (4)
N1—C1	1.316 (4)	C11—C12	1.390 (4)
N1—H1N1	0.8800	C12—C13	1.369 (4)
N1—H1N2	0.8800	C12—H12	0.9500
N2—C1	1.341 (4)	C13—C14	1.396 (4)
N2—N3	1.375 (3)	C14—C15	1.375 (4)
N2—H2N	0.8800	C15—C16	1.385 (4)
N3—C2	1.269 (4)	C15—H15	0.9500
N4—C9	1.316 (4)	C16—H16	0.9500
N4—H4N1	0.8800	C18—C19	1.457 (4)
N4—H4N2	0.8800	C18—H18	0.9500
N5—C9	1.335 (4)	C19—C24	1.384 (4)
N5—N6	1.377 (3)	C19—C20	1.397 (4)
N5—H5N	0.8800	C20—C21	1.368 (4)
N6—C10	1.276 (4)	C20—H20	0.9500
N7—C17	1.316 (4)	C21—C22	1.390 (4)
N7—H7N1	0.8800	C22—C23	1.380 (4)
N7—H7N2	0.8800	C23—C24	1.386 (4)
N8—C17	1.344 (4)	C23—H23	0.9500
N8—N9	1.380 (3)	C24—H24	0.9500
N8—H8N	0.8800
C5—O1—H1O	115 (3)	C3—C8—H8	119.6
C6—O2—H2O	107 (3)	N4—C9—N5	116.7 (3)
C13—O3—H3O	106 (4)	N4—C9—S2	123.5 (2)
C14—O4—H4O	107 (3)	N5—C9—S2	119.8 (2)
C21—O5—H5O	103 (3)	N6—C10—C11	121.2 (3)
C22—O6—H6O	112 (3)	N6—C10—H10	119.4
C1—N1—H1N1	120.0	C11—C10—H10	119.4
C1—N1—H1N2	120.0	C16—C11—C12	119.0 (3)
H1N1—N1—H1N2	120.0	C16—C11—C10	118.9 (3)
C1—N2—N3	118.9 (3)	C12—C11—C10	122.0 (3)
C1—N2—H2N	120.5	C13—C12—C11	120.3 (3)
N3—N2—H2N	120.5	C13—C12—H12	119.8
C2—N3—N2	116.4 (3)	C11—C12—H12	119.8
C9—N4—H4N1	120.0	O3—C13—C12	118.8 (3)
C9—N4—H4N2	120.0	O3—C13—C14	120.7 (3)
H4N1—N4—H4N2	120.0	C12—C13—C14	120.5 (3)
C9—N5—N6	118.9 (3)	O4—C14—C15	124.2 (3)
C9—N5—H5N	120.6	O4—C14—C13	116.4 (3)
N6—N5—H5N	120.6	C15—C14—C13	119.4 (3)
C10—N6—N5	116.1 (3)	C14—C15—C16	120.0 (3)
C17—N7—H7N1	120.0	C14—C15—H15	120.0
C17—N7—H7N2	120.0	C16—C15—H15	120.0
H7N1—N7—H7N2	120.0	C15—C16—C11	120.6 (3)
C17—N8—N9	119.0 (3)	C15—C16—H16	119.7
C17—N8—H8N	120.5	C11—C16—H16	119.7
N9—N8—H8N	120.5	N7—C17—N8	115.9 (3)
C18—N9—N8	115.9 (3)	N7—C17—S3	124.0 (3)
N1—C1—N2	116.6 (3)	N8—C17—S3	120.0 (3)
N1—C1—S1	123.3 (2)	N9—C18—C19	121.1 (3)
N2—C1—S1	120.1 (2)	N9—C18—H18	119.5
N3—C2—C3	121.7 (3)	C19—C18—H18	119.5
N3—C2—H2	119.2	C24—C19—C20	118.6 (3)
C3—C2—H2	119.2	C24—C19—C18	119.6 (3)
C4—C3—C8	118.5 (3)	C20—C19—C18	121.8 (3)
C4—C3—C2	122.7 (3)	C21—C20—C19	120.4 (3)
C8—C3—C2	118.8 (3)	C21—C20—H20	119.8
C5—C4—C3	120.7 (3)	C19—C20—H20	119.8
C5—C4—H4	119.7	O5—C21—C20	119.0 (3)
C3—C4—H4	119.7	O5—C21—C22	120.3 (3)
O1—C5—C4	118.7 (3)	C20—C21—C22	120.6 (3)
O1—C5—C6	121.0 (3)	O6—C22—C23	123.8 (3)
C4—C5—C6	120.3 (3)	O6—C22—C21	116.6 (3)
O2—C6—C7	123.0 (3)	C23—C22—C21	119.6 (3)
O2—C6—C5	117.1 (3)	C22—C23—C24	119.5 (3)
C7—C6—C5	119.9 (3)	C22—C23—H23	120.2
C6—C7—C8	119.8 (3)	C24—C23—H23	120.2
C6—C7—H7C	120.1	C19—C24—C23	121.2 (3)
C8—C7—H7C	120.1	C19—C24—H24	119.4
C7—C8—C3	120.8 (3)	C23—C24—H24	119.4
C7—C8—H8	119.6
C1—N2—N3—C2	−176.9 (3)	C11—C12—C13—C14	−1.3 (5)
C9—N5—N6—C10	−175.5 (3)	O3—C13—C14—O4	1.2 (5)
C17—N8—N9—C18	179.2 (3)	C12—C13—C14—O4	−177.4 (3)
N3—N2—C1—N1	5.5 (5)	O3—C13—C14—C15	−177.8 (3)
N3—N2—C1—S1	−175.4 (2)	C12—C13—C14—C15	3.7 (5)
N2—N3—C2—C3	−177.5 (3)	O4—C14—C15—C16	178.4 (3)
N3—C2—C3—C4	2.9 (5)	C13—C14—C15—C16	−2.7 (5)
N3—C2—C3—C8	−179.7 (3)	C14—C15—C16—C11	−0.5 (5)
C8—C3—C4—C5	−0.8 (5)	C12—C11—C16—C15	2.9 (5)
C2—C3—C4—C5	176.6 (3)	C10—C11—C16—C15	−173.6 (3)
C3—C4—C5—O1	−179.9 (3)	N9—N8—C17—N7	3.0 (5)
C3—C4—C5—C6	−0.4 (5)	N9—N8—C17—S3	−177.6 (2)
O1—C5—C6—O2	0.4 (5)	N8—N9—C18—C19	−177.0 (3)
C4—C5—C6—O2	−179.1 (3)	N9—C18—C19—C24	−176.7 (3)
O1—C5—C6—C7	−179.3 (3)	N9—C18—C19—C20	5.3 (5)
C4—C5—C6—C7	1.2 (5)	C24—C19—C20—C21	−2.5 (5)
O2—C6—C7—C8	179.5 (3)	C18—C19—C20—C21	175.5 (3)
C5—C6—C7—C8	−0.9 (5)	C19—C20—C21—O5	−176.6 (3)
C6—C7—C8—C3	−0.3 (5)	C19—C20—C21—C22	1.1 (5)
C4—C3—C8—C7	1.1 (5)	O5—C21—C22—O6	−1.2 (5)
C2—C3—C8—C7	−176.4 (3)	C20—C21—C22—O6	−178.8 (3)
N6—N5—C9—N4	0.9 (5)	O5—C21—C22—C23	179.0 (3)
N6—N5—C9—S2	179.8 (2)	C20—C21—C22—C23	1.4 (5)
N5—N6—C10—C11	−176.7 (3)	O6—C22—C23—C24	177.8 (3)
N6—C10—C11—C16	175.3 (3)	C21—C22—C23—C24	−2.5 (5)
N6—C10—C11—C12	−1.1 (5)	C20—C19—C24—C23	1.4 (5)
C16—C11—C12—C13	−2.0 (5)	C18—C19—C24—C23	−176.6 (3)
C10—C11—C12—C13	174.4 (3)	C22—C23—C24—C19	1.0 (5)
C11—C12—C13—O3	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O6i	0.84 (1)	2.07 (3)	2.784 (3)	143 (4)
O2—H2o···S1ii	0.84 (1)	2.47 (1)	3.300 (2)	171 (4)
N1—H1n2···O5iii	0.88	2.00	2.856 (4)	163
O3—H3o···O4i	0.84 (1)	2.11 (4)	2.732 (3)	130 (4)
O4—H4o···S2ii	0.84 (1)	2.38 (1)	3.219 (2)	174 (4)
N4—H4n2···O3iii	0.88	2.05	2.900 (4)	162
O5—H5o···O2i	0.84 (1)	2.16 (4)	2.742 (3)	127 (4)
O6—H6o···S3ii	0.84 (1)	2.40 (1)	3.244 (2)	177 (4)
N7—H7n2···O1iii	0.88	2.13	2.981 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O6i	0.84 (1)	2.07 (3)	2.784 (3)	143 (4)
O2—H2o⋯S1ii	0.84 (1)	2.47 (1)	3.300 (2)	171 (4)
N1—H1n2⋯O5iii	0.88	2.00	2.856 (4)	163
O3—H3o⋯O4i	0.84 (1)	2.11 (4)	2.732 (3)	130 (4)
O4—H4o⋯S2ii	0.84 (1)	2.38 (1)	3.219 (2)	174 (4)
N4—H4n2⋯O3iii	0.88	2.05	2.900 (4)	162
O5—H5o⋯O2i	0.84 (1)	2.16 (4)	2.742 (3)	127 (4)
O6—H6o⋯S3ii	0.84 (1)	2.40 (1)	3.244 (2)	177 (4)
N7—H7n2⋯O1iii	0.88	2.13	2.981 (4)	161

Symmetry codes: (i) ; (ii) ; (iii) .